Dimethyl Sulfoxide → HCID 178501146, compound

HRID 131257Notes

Reaction equation

HRID 131257 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]1.C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl>[CH:12]([C@H:13]1[CH2:14][CH2:15][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]1)=[O:11]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178501147HCID 178501147, compound

Product 1

HCID 178501146HCID 178501146, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of oxalyl chloride (4.48 mL) in methylene chloride (50 mL) is added dropwise dimethylsulfoxide (4.55 g) in methylene chloride (5 mL) at −60° C. over a period of 15 minutes. To the mixture is added dropwise a solution of methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (compound obtained in Reference Example 238; 5.9 g) in methylene chloride (30 mL) over a period of 30 minutes. The mixture is stirred at the same temperature for 1 hour and thereto is added dropwise triethylamine (16.7 mL) at −60° C. The mixture is stirred at the same temperature for 30 minutes and at 0° C. for 1 hour. The reaction mixture is diluted with chloroform, and washed successively with water, 5% citric acid solution, water, and saturated brine. The organic layer is dried over anhydrous sodium sulfate and concentrated in vacuo to give methyl trans-4-formylcyclohexanecarboxylate (5.32 g, yield; 91%) as an oil.

Workup

  1. stirringThe mixture is stirred at the same temperature for 30 minutes and at 0° C. for 1 hour
  2. washwashed successively with water, 5% citric acid solution, water, and saturated brine
  3. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-00de2bc6a02f4d98b6c76998d1aaa560
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

Loading…